The present invention relates to antibacterial agents of the carbapenem class, in which the 2-position sidechain is characterized by a phenyl moiety, optionally substituted, to which is attached, usually through an alkyl bridge, a nitrogen-containing quinolinium or isoquinolinium group, with attachment being through the nitrogen atom, which may, in turn, be substituted.
Thienamycin was an early carbapenem antibacterial agent having a broad spectrum; it has the following formula: ##STR2##
Later, N-formimidoyl thienamycin was discovered; it has the formula: ##STR3##
The 2-(quinoliniumalkyl and isoquinolinium-alkyl) phenyl carbapenems of the present invention have an antibacterial potency equal to or greater than, in most cases, that of either thienamycin or N-formimidoyl thienamycin. The compounds of the present invention are also more resistant than thienamycin or N-formimidoyl thienamycin to degradation by the dehydropeptidase enzyme DHP-I, thus permitting greater therapeutic application of the compounds.
More recently, carbapenem antibacterial agents have been described which have a 2-substituent which is an aryl moiety optionally substituted by, e.g., aminomethyl and substituted aminomethyl. These agents are described in U.S. Pat. Nos. 4,543,257 and 4,260,627 and have the formula: ##STR4##
However, these compounds belong to a different class from those of the present invention and are distinguished by different physiological properties.